Pyridine → 6-Phenoxypyrid-2-ylmethyl 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane carboxylate

HRID 231844Notes

Reaction equation

HRID 231844 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:18](Cl)=[O:19])[CH2:13][C:12]([F:15])([F:14])[C:11]2([F:17])[F:16])=[CH:6][CH:5]=1)[CH3:2].[OH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:24]=1.N1C=CC=CC=1>C1C=CC=CC=1.CCOCC>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:24]=3)=[O:19])[CH2:13][C:12]([F:15])([F:14])[C:11]2([F:16])[F:17])=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 128791556-Phenoxy-2-pyridinemethanolHCID 135589381-(4-Ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane-1-carbonyl chloride

Product 1

HCID 200321336-Phenoxypyrid-2-ylmethyl 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane carboxylate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane carbonyl chloride (0.76 gm, 1.54 mmole) in dry benzene (10 ml) was added a solution of 2-hydroxymethyl-6-phenoxypyridine (0.305 g) and pyridine (0.12 g) in dry benzene (15 ml). The mixture was stirred at room temperature for 16 hours then diluted with ether, washed twice with water, dried over Na2SO4 and concentrated in vacuo. Purification by high pressure liquid chromatography gave the ester as a colourless oil. IR (film) λmax 1741, 1606, 1591, 1575, 1500, 1490, 1450 cm-1. N.m.r. (250 MHz) δ (CDCl3) 1.42, t, 3H, J=7 Hz, CH3 ; 2.90-3.08, m, 1H, cyclobutyl H; 3.44-3.64, m, 1H, cyclobutyl H; 4.02, q, 2H, J=7 Hz, CH2CH3 ; 5.10, 5.16, ABq, 2H, J=14.5 Hz, CH2 -O; 6.71-7.64, m, 13H, aromatic H's. Mass spectrum, m/z 476 (M+ +1), 456 (M+ -19).

Workup

  1. washwashed twice with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification by high pressure liquid chromatography

Sources & evidence

ORD record
ord-ace76d447b274dc58d478e5b7e2c3b92
Source dataset
uspto-grants-1989_07
Patent number
US04849450

Reaction notes

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